US4948506AExpiredUtility

Physicochemically functional ultrathin films by interfacial polymerization

85
Assignee: BEND RES INCPriority: Jul 7, 1986Filed: Nov 14, 1988Granted: Aug 14, 1990
Est. expiryJul 7, 2006(expired)· nominal 20-yr term from priority
Inventors:Harold K. LonsdaleWalter C. BabcockDwayne T. FriensenKelly L. SmithBruce JohnsonCarl C. Wamser
B01D 69/1251B01D 71/82B01J 2531/0252B01J 2531/847B01J 31/2243C08G 69/42B01J 2531/845G01N 27/3271H01M 4/60B01J 31/226B01D 69/122C01B 13/0255B01J 31/182B01J 2531/842C01B 13/0262H01G 9/20B01J 31/183B01J 2531/821C01B 2210/0046B01J 31/223B01J 2531/025B01J 13/16H01M 14/005B01D 71/56B01J 20/28033B01J 2531/16B01J 31/1815B01J 2531/822C08G 85/00Y02E60/10B01J 35/59
85
PatentIndex Score
61
Cited by
1
References
36
Claims

Abstract

Interfacially-polymerized ultrathin films containing physicochemically functional groups are disclosed, both with and without supports. Various applications are disclsoed, including membrane electrodes, selective membranes and sorbents, biocompatible materials, targeted drug delivery, and narrow band optical absorbers.

Claims

exact text as granted — not AI-modified
What is claimed is: 
     
       1. A composition of matter comprising the thin film interfacial polymerization reaction product of M F  X m  and NY n  wherein M F  is a moiety having chemical species-specific reversibly-complexing complexing sites, N is a moiety not having any chemical species-specific complexing sites, X and Y are groups that are mutually reactive in a condensation reaction, and m and n are integers ≧2. 
     
     
       2. The composition of matter of claim 1 wherein X and Y are selected from acid halides, amines, aldehydes, alcohols, thiols, isocyanates and sulfonyl halides. 
     
     
       3. The composition of matter of claim 1 wherein M F  is selected from organophosphoryl, cyclic crown ether, metalloporphyrin, metallo-Schiff base, metallophthalocyanine, macrocyclic metallobeta-diketone, pyrrolidone, metallocyclic ether, metallocyclic thioether, metallopolyazamacrocycle, and metallosulfonate. 
     
     
       4. The composition of matter of claim 3 wherein said metallo-Schiff base is selected from the structures ##STR31## wherein M is a metal of +2 valence selected from cobalt, iron, copper, nickel, manganese, ruthenium and rhodium; X is ##STR32## and R is hydrogen, alkyl, aryl, arylene halogen, alkoxy or a nitrogen-containing moiety. 
     
     
       5. The composition of matter of claim 3 wherein the metal of said metalloporphyrin, said metallo-Schiff base and said metallophthaloxcyanine is selected from cobalt (II) and iron (II). 
     
     
       6. The composition of matter of claim 5 comprising the interfacial polymerization reaction product of tetra-(aminophenyl)-porphyrin iron(II) and a polyacyl halide. 
     
     
       7. The composition of matter of claim 6 wherein the polyacyl halide is selected from fumaryl chloride and tetra-(carboxyphenyl acid chloride)porphyrin iron(II). 
     
     
       8. The composition of matter of claim 3 wherein said pyrrolidone is of the formula ##STR33## wherein R' is hydrogen, alkyl, aryl, cycloalkyl, substituted alkyl, substituted aryl, or substituted cycloalkyl; and R" is alkyl or substituted alkyl. 
     
     
       9. The composition of matter of claim 8 wherein said pyrrolidone is selected from N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, 5-methyl-N-cyclohexyl-2-pyrrolidone, N-tallowalkyl-2-pyrrolidone, and N-cocoalkyl-2-pyrrolidone. 
     
     
       10. The composition of matter of claim 1 wherein M F  is ##STR34## X is --NH 2  ; N is aryl; Y is --COHal or --NCO; m and n are 2 or 3; R is selected from hydrogen, alkyl and aryl; R' is a covalent bond or alkylene; Hal is halide. 
     
     
       11. The composition of matter of claim 1 wherein M F  is dibenzo-18-crown-6; X is --NH 2  ; N is aryl; and Y is selected from acid halides and isocyanates. 
     
     
       12. The composition of matter of claim 11 wherein said acid halide is selected from isophthaloyl chloride, terephthaloyl chloride and trimesoyl chloride. 
     
     
       13. The composition of matter of claim 11 wherein said isocyanate is tolyldiisocyanate. 
     
     
       14. The composition of matter of claim 1, comprising the interfacial polymerization reaction product of (a) a tetraazamacrocylic compound selected from the structures ##STR35## wherein R is hydrogen, alkyl containing from 1 to 20 carbon atoms, or aryl, and   (b) a polyacyl halide.   
     
     
       15. The composition of matter of claim 1 comprising the interfacial polymerization reaction product of a thioimino cryptand having the structure ##STR36## and a polyacyl halide. 
     
     
       16. The composition of matter of claim 7 comprising the interfacial polymerization reaction product of a diamino macrocylic acetylacetone copper (II) ligand having the structure ##STR37## and a diacid halide. 
     
     
       17. The composition of matter of claim 1 comprising the metal ion sulfonate complex of the interfacial polymerization reaction product of tolyl diisocyanate sulfonate and a diol, said metal ion being selected from copper (I) and silver (I). 
     
     
       18. The composition of matter of claim 17 wherein said diol is diethylene glycol. 
     
     
       19. A composite selective membrane comprising a microporous support and the thin film interfacial polymerization reaction product of M F  X m  and NY n  wherein M F  is a moiety having chemical species-specific reversibly-complexing complexing sites, N is a moiety not having any chemical species-specific complexing sites, X and Y are groups that are mutually reactive in a condensation reaction, and m and n are integers ≧2. 
     
     
       20. The composite selective membrane of claim 19 wherein X and Y are selected from acid halides, amines, aldehydes, alcohols, thiols, isocyanates and sulfonyl halides. 
     
     
       21. The composite selective membrane of claim 19 wherein M F  is selected from organophosphoryl, cyclic crown ether, metalloporphyrin, metallo-Schiff base, metallophthalocyanine, macrocyclic metallobeta-diketone, pyrrolidone, metallocyclic ether, metallocyclic thioether, metallopolyazamacrocycle, and metallosulfonate. 
     
     
       22. The composite selective membrane of claim 21 wherein said metallo-Schiff base is selected from the structures ##STR38## wherein M is a metal of +2 valence selected from cobalt, iron, copper, nickel, manganese, ruthenium and rhodium; X is ##STR39## and R is hydrogen, alkyl, aryl, arylene halogen, alkoxy or a nitrogen-containing moiety. 
     
     
       23. The composite selective membrane of claim 21 wherein the metal of said metalloporphyrin, said metallo-Schiff base and said metallophthalocyanine is selected from cobalt(II) and iron(II). 
     
     
       24. The composite selective membrane of claim 23 comprising the interfacial polymerization reaction product of tetra-(aminophenyl)-porphyrin iron(II) and a polyacyl halide. 
     
     
       25. The composite selective membrane of claim 24 wherein the polyacyl halide is selected from fumaryl chloride and tetra-(carboxyphenyl acid chloride)-porphyrin iron(II). 
     
     
       26. The composite selective membrane of claim 21 wherein said pyrrolidone is of the formula ##STR40## wherein R' is hydrogen or R"; R" is aklyl, aryl, cycloalkyl, substituted alkyl, substituted aryl, or substituted cycloalkyl. 
     
     
       27. The composite selective membrane of claim 26 wherein said pyrrolidone is selected from N-methyl-2-pyrrolidone, N-cyclohexyl-2-pyrrolidone, 5-methyl-N-cyclohexyl-2-pyrrolidone, N-tallowalkyl-2-pyrrolidone, and N-cocoalkyl-2pyrrolidone. 
     
     
       28. The composite selective membrane of claim 19 wherein M F  is ##STR41## X is --NH 2  ; N is aryl; Y is --COHal or --NCO; m and n are 2 or 3; R is selected from hydrogen, alkyl and aryl; R' is a covalent bond or alkylene; and Hal is halide. 
     
     
       29. The composite selective membrane of claim 19 wherein M F  is dibenzo-18-crown-6; X is --NH 2  ; N is aryl; and Y is selected from acid halides and isocyanates. 
     
     
       30. The composite selective membrane of claim 29 wherein said acid halide is selected from isophthaloyl chloride, terephthaloyl chloride and trimesoyl chloride. 
     
     
       31. The composite selective membrane of claim 29 wherein said isocyanate is tolyldiisocyanate. 
     
     
       32. The composite selective membrane of claim 19 wherein (a) M F  X m  is a tetraazamacrocylic compound selected from the structures ##STR42## wherein R is hydrogen, alkyl containing from 1 to 20 carbon atoms, or aryl, and   (b) NY n  is a polyacyl halide.   
     
     
       33. The composite selective membrane of claim 19 wherein M F  X m  is a thioimino cryptand having the structure ##STR43## and NY n  is a polyacyl halide. 
     
     
       34. The composite selective membrane of claim 19 wherein M F  X m  is a diamino macrocylic acetylacetone copper(II) ligand having the structure ##STR44## and NY n  is a polyacyl halide. 
     
     
       35. The composite selective membrane of claim 19 wherein said thin film interfacial polymerization reaction product is of tolyl diisocyanate sulfonate and a diol, said metal ion being selected from copper (I) and silver (I). 
     
     
       36. The composite selective membrane of claim 35 wherein said diol is ethylene glycol.

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